Personally, I love Rubedo's game sense of humor, but not everyone can pull off such a look. Check out this Darkmoon Faire-esque look on Mathryn of Wyrmrest Accord. There's nothing overtly goofy about it, but I'm afraid my main would feel foolish questing and doing business in town looking like a carnie. I'd wear it in a heartbeat on the right alt, but wearing something this offbeat on a full-time basis feels awkward to me.
How far are you willing to take your daily mog? Do you want an look that lends your character dignity or deepens your immersion, or are you more interested in poking a bit of fun at the whole thing? How silly do things have to get before you start feeling a little ridiculous?